AU624585B2 - Heterocyclic compounds - Google Patents
Heterocyclic compounds Download PDFInfo
- Publication number
- AU624585B2 AU624585B2 AU25342/88A AU2534288A AU624585B2 AU 624585 B2 AU624585 B2 AU 624585B2 AU 25342/88 A AU25342/88 A AU 25342/88A AU 2534288 A AU2534288 A AU 2534288A AU 624585 B2 AU624585 B2 AU 624585B2
- Authority
- AU
- Australia
- Prior art keywords
- signifies
- alkyl
- chloro
- ppm
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 54
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 241000196324 Embryophyta Species 0.000 claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims description 102
- -1 isopropylideneamino Chemical group 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- 239000001257 hydrogen Substances 0.000 claims description 65
- 150000002084 enol ethers Chemical class 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 33
- 239000013543 active substance Substances 0.000 claims description 25
- 235000010233 benzoic acid Nutrition 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 239000005711 Benzoic acid Substances 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 150000002923 oximes Chemical class 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 238000009472 formulation Methods 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 150000001559 benzoic acids Chemical class 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims 1
- 241001136792 Alle Species 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 150000004292 cyclic ethers Chemical class 0.000 description 8
- 239000004495 emulsifiable concentrate Substances 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000002612 dispersion medium Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- GABPINBCLIZKHD-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoic acid Chemical compound COC1=NC(C(F)(F)F)=CC(=O)N1C1=CC(C(O)=O)=C(Cl)C=C1F GABPINBCLIZKHD-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000001117 sulphuric acid Substances 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000002363 herbicidal effect Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 2
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
- WFDLOUDEDOLTLC-UHFFFAOYSA-N 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoic acid Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC(C(O)=O)=C(Cl)C=C1F WFDLOUDEDOLTLC-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
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- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- SXMJZBWKZMLWIJ-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-[2-methoxy-6-oxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound COC1=NC(C(F)(F)F)=CC(=O)N1C1=CC(C(=O)OC(C)C)=C(Cl)C=C1F SXMJZBWKZMLWIJ-UHFFFAOYSA-N 0.000 description 1
- UAHXBOAKPTWXNS-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-isocyanatobenzoate Chemical compound CC(C)OC(=O)C1=CC(N=C=O)=C(F)C=C1Cl UAHXBOAKPTWXNS-UHFFFAOYSA-N 0.000 description 1
- COSBNVAHJWHDBT-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[2,4-dioxo-6-(trifluoromethyl)-1h-pyrimidin-3-yl]-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(NC(=CC2=O)C(F)(F)F)=O)=C1F COSBNVAHJWHDBT-UHFFFAOYSA-N 0.000 description 1
- AXZSMISENXTDQW-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-(difluoromethyl)-4-methyl-2,6-dioxopyrimidin-1-yl]-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C(F)F)C(C)=CC2=O)=O)=C1F AXZSMISENXTDQW-UHFFFAOYSA-N 0.000 description 1
- 108700023468 protein-bound SN-C polysaccharide Proteins 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- RHZFPUHJKLDBBS-UHFFFAOYSA-N s-phenyl 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzenecarbothioate Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC(C(=O)SC=2C=CC=CC=2)=C(Cl)C=C1F RHZFPUHJKLDBBS-UHFFFAOYSA-N 0.000 description 1
- IBAZPXCZVWEHIF-UHFFFAOYSA-N s-propan-2-yl 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzenecarbothioate Chemical compound C1=C(Cl)C(C(=O)SC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F IBAZPXCZVWEHIF-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Soil Working Implements (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH413287 | 1987-10-22 | ||
| CH4132/87 | 1987-10-22 | ||
| PCT/CH1988/000197 WO1989003825A1 (en) | 1987-10-22 | 1988-10-21 | Heterocyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2534288A AU2534288A (en) | 1989-05-23 |
| AU624585B2 true AU624585B2 (en) | 1992-06-18 |
Family
ID=4270431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU25342/88A Ceased AU624585B2 (en) | 1987-10-22 | 1988-10-21 | Heterocyclic compounds |
Country Status (12)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084084A (en) * | 1989-07-14 | 1992-01-28 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| AU627906B2 (en) * | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| US5134145A (en) * | 1989-11-17 | 1992-07-28 | Uniroyal Chemical Company, Inc. | Pesticidal pyrimidinyl benzoic acids and esters |
| EP0473551A1 (de) * | 1990-08-31 | 1992-03-04 | Ciba-Geigy Ag | 3-Aryluracil-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Unkrautbekämpfungsmittel |
| US5266554A (en) * | 1990-08-31 | 1993-11-30 | Ciba-Geigy Corporation | Heterocyclic compounds |
| BR9104045A (pt) * | 1990-09-21 | 1992-06-09 | Sumitomo Chemical Co | Composto,processos para sua preparacao,composto intermediario,composicao herbicida,processo para exterminio de ervas daninhas indesejadas e uso do dito primeiro composto |
| GB9022444D0 (en) * | 1990-10-16 | 1990-11-28 | Ici Plc | Heterocyclic compounds |
| EP0489480A1 (en) * | 1990-12-05 | 1992-06-10 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| JP3089621B2 (ja) * | 1990-12-17 | 2000-09-18 | 日産化学工業株式会社 | ウラシル誘導体 |
| US5169430A (en) * | 1991-08-09 | 1992-12-08 | Uniroyal Chemical Company, Inc. | Benzenesulfonamide derivatives and methods for their production |
| DE4131038A1 (de) * | 1991-09-20 | 1993-04-01 | Basf Ag | Substituierte 3-phenylurazile |
| JPH05125057A (ja) * | 1991-11-01 | 1993-05-21 | Sumitomo Chem Co Ltd | １−フエニル−４−トリフルオロメチルウラシル誘導体およびそれを有効成分とする除草剤 |
| EP0542685A1 (de) * | 1991-11-13 | 1993-05-19 | Ciba-Geigy Ag | Neue 3-Aryluracil-Derivate und deren Verwendung zur Unkrautbekämpfung |
| DE4140661A1 (de) * | 1991-12-10 | 1993-06-17 | Basf Ag | Verwendung von 3-phenylurazil-derivaten zur desikkation und abzission von pflanzenteilen |
| BR9301666A (pt) * | 1992-04-28 | 1993-11-03 | Sumitomo Chemical Co | Composto,composto intermediario,composicao herbicida,processo para exterminar ervas daninhas indesejadas,uso do dito composto e processo para produzi-lo |
| US5521144A (en) * | 1992-09-18 | 1996-05-28 | Central Soya Company, Inc. | Herbicide composition |
| BR9305683A (pt) * | 1992-10-23 | 1996-12-03 | Ciba Geigy Ag | Derivados de 3-ariluracila e o uso dos mesmos para controle de ervas daninhas |
| US5399543A (en) * | 1993-04-21 | 1995-03-21 | Fmc Corporation | 3-[4-(phenylmethoxy)phenyl]-1-substituted-6-haloalkyl-uracil herbicides |
| US5346881A (en) * | 1993-08-13 | 1994-09-13 | Fmc Corporation | 2-(bicyclic heterocyclyl)-6-fluoroalkyluracils |
| CA2156652A1 (en) * | 1994-08-31 | 1996-03-01 | Minoru Takano | Epoxyphenol derivatives and herbicides containing them as active ingredients |
| DE19649094A1 (de) * | 1996-11-27 | 1998-05-28 | Bayer Ag | Phenyl-uracil-Derivate |
| CA2269627A1 (en) * | 1997-08-25 | 1999-03-04 | Itsuo Nagai | Polyester film for electrical insulation |
| JP4639459B2 (ja) * | 1999-11-01 | 2011-02-23 | 住友化学株式会社 | ６−ヒドロキシ−５，６−ジヒドロウラシル化合物 |
| PL375299A1 (en) * | 2002-07-23 | 2005-11-28 | Basf Aktiengesellschaft | 3-heterocyclyl substituted benzoic acid derivatives |
| CN100360509C (zh) * | 2005-04-15 | 2008-01-09 | 南开大学 | 用作除草剂的1-嘧啶酮基-4-氯-5-苯甲酸酯类化合物及其制备方法 |
| CN110078673B (zh) * | 2019-05-31 | 2020-04-24 | 深圳大学 | 一种芳基尿嘧啶类化合物及其制备方法和农药组合物 |
| CN114656407B (zh) * | 2020-12-23 | 2023-06-16 | 帕潘纳(北京)科技有限公司 | 一种制备苯嘧磺草胺中间体的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0195346A2 (de) * | 1985-03-20 | 1986-09-24 | Ciba-Geigy Ag | 3-Aryluracile und deren Verwendung zur Unkrautbekämpfung |
| AU7637187A (en) * | 1986-07-31 | 1988-02-11 | Ciba-Geigy Ag | 3-phenyl-2,4(1H,3H)-pyrimidinediones |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3137698A (en) * | 1964-06-16 | New uracil derivatives | ||
| US4266056A (en) * | 1978-04-07 | 1981-05-05 | Zoecon Corporation | Phenyl uracils |
| EP0260621A3 (de) * | 1986-09-18 | 1989-03-15 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | 3-Aryluracil-enoläther und deren Verwendung zur Unkrautbekämpfung |
| US4927451A (en) * | 1988-12-30 | 1990-05-22 | Uniroyal Chemical Company, Inc. | 3-aryldihydrouracils |
-
1988
- 1988-10-21 JP JP63508016A patent/JPH02501831A/ja active Pending
- 1988-10-21 KR KR1019890701132A patent/KR890701568A/ko not_active Ceased
- 1988-10-21 BR BR888807266A patent/BR8807266A/pt not_active Application Discontinuation
- 1988-10-21 HU HU885892A patent/HU207932B/hu not_active IP Right Cessation
- 1988-10-21 AU AU25342/88A patent/AU624585B2/en not_active Ceased
- 1988-10-21 HU HU885892A patent/HUT51864A/hu unknown
- 1988-10-21 AT AT88908651T patent/ATE87308T1/de not_active IP Right Cessation
- 1988-10-21 DE DE8888908651T patent/DE3879681D1/de not_active Expired - Fee Related
- 1988-10-21 US US07/369,557 patent/US5041156A/en not_active Expired - Fee Related
- 1988-10-21 WO PCT/CH1988/000197 patent/WO1989003825A1/de active IP Right Grant
- 1988-10-21 EP EP88908651A patent/EP0344232B1/de not_active Expired - Lifetime
-
1989
- 1989-06-21 DK DK307289A patent/DK167014B1/da not_active IP Right Cessation
- 1989-06-21 NO NO89892579A patent/NO892579L/no unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0195346A2 (de) * | 1985-03-20 | 1986-09-24 | Ciba-Geigy Ag | 3-Aryluracile und deren Verwendung zur Unkrautbekämpfung |
| AU5498186A (en) * | 1985-03-20 | 1986-09-25 | Ciba-Geigy Ag | Improvements in or relating to 3-Aryluracils |
| AU7637187A (en) * | 1986-07-31 | 1988-02-11 | Ciba-Geigy Ag | 3-phenyl-2,4(1H,3H)-pyrimidinediones |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02501831A (ja) | 1990-06-21 |
| DE3879681D1 (de) | 1993-04-29 |
| WO1989003825A1 (en) | 1989-05-05 |
| NO892579D0 (no) | 1989-06-21 |
| EP0344232A1 (de) | 1989-12-06 |
| EP0344232B1 (de) | 1993-03-24 |
| BR8807266A (pt) | 1989-10-31 |
| DK307289A (da) | 1989-06-21 |
| HUT51864A (enrdf_load_html_response) | 1990-06-28 |
| HU207932B (en) | 1993-07-28 |
| NO892579L (no) | 1989-06-21 |
| ATE87308T1 (de) | 1993-04-15 |
| DK167014B1 (da) | 1993-08-16 |
| HU885892D0 (en) | 1990-05-28 |
| DK307289D0 (da) | 1989-06-21 |
| US5041156A (en) | 1991-08-20 |
| KR890701568A (ko) | 1989-12-21 |
| AU2534288A (en) | 1989-05-23 |
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